Heterocyclic compound and resistant harmful arthropod- controlling method for composition containing same

Abstract

The present invention provides a compound that has an excellent efficacy for controlling resistant harmful arthropods, a composition comprising the compound, and a method using the compound or the composition. A compound represented by formula (I) [wherein R 1 represents a C1-C6 chain hydrocarbon group, etc., R 3 and R 7 each represents a hydrogen atom, etc., R 4 and R 6 each represents a hydrogen atom, etc., R 5 represent a hydrogen atom, etc., Q represents a group represented by Q1, etc. (where # represents a binding site to a pyridine ring, and ● represents a binding site to a benzene ring), A 1 represents a nitrogen atom, etc., A 2 represents a nitrogen atom, etc., and A 3 represents a nitrogen atom, etc.] or its N-oxide, or salts thereof has an excellent efficacy on controlling resistant harmful arthropods.

1 : A method for controlling a resistant harmful arthropod which comprises applying an effective amount of a compound represented by formula (I): 
       
         
           
           
               
               
           
         
         [wherein 
         R 1  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group (the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be optionally substituted with one or more substituents selected from Group A), a C3-C7 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C3-C7 cycloalkenyl group, a phenyl group, a three- to seven-membered nonaromatic heterocyclic group, a five- or six-membered aromatic heterocyclic group (the C3-C7 cycloalkenyl group, the phenyl group, the three- to seven-membered nonaromatic heterocyclic group, and the five- or six-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C), a nitro group, NR 8 R 9 , S(O) m R 10 , or a halogen atom, 
         m is 0, 1 or 2, 
         R 2  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group (the C1-C6 chain hydrocarbon group and the C1-C6 alkoxy group may be optionally substituted with one or more substituents selected from Group A), a C3-C7 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a C3-C7 cycloalkenyl group, a phenyl group, a three- to seven-membered nonaromatic heterocyclic group, a five- or six-membered aromatic heterocyclic group (the C3-C7 cycloalkenyl group, the phenyl group, the three- to seven-membered nonaromatic heterocyclic group, and the five- or six-membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group C), a nitro group, NR 8a R 9a , S(O) n R 10a , a halogen atom, or a hydrogen atom, 
         n is 0, 1 or 2, 
         R 3  and R 7  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, 
         R 4  and R 6  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C3-C6 cycloalkyl group, a phenyl group, a five- or six-membered aromatic heterocyclic group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C3-C6 alkenyloxy group, the C3-C6 alkynyloxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, the C3-C6 cycloalkyl group, the phenyl group, and the five- or six-membered aromatic heterocyclic group may be optionally substituted with one or more halogen atoms), a cyano group, a nitro group, a halogen atom, or a hydrogen atom, 
         R 5  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C3-C6 alkenyloxy group, the C3-C6 alkynyloxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, and the C1-C6 alkylsulfonyl group may be optionally substituted with one or more halogen atoms), a nitro group, a halogen atom, or a hydrogen atom, 
         R 8  and R 8a  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom, 
         R 9  and R 9a  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group, a C3-C7 cycloalkyl group, a C3-C7 cycloalkenyl group (the C1-C6 chain hydrocarbon group, the C3-C7 cycloalkyl group and the C3-C7 cycloalkenyl group may be optionally substituted with one or more substituents selected from Group C), or a hydrogen atom, 
         R 10  and R 10a  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, 
         Q represents a group represented by Q1, a group represented by Q2, a group represented by Q3, or a group represented by Q4 (where # represents a binding site to a pyridine ring, and ● represents a binding site to a benzene ring), 
       
       
         
           
           
               
               
           
         
         A1 represents a nitrogen atom, or CR 11 , 
         A2 represents an oxygen atom, a sulfur atom, or NR 12 , 
         A3 represents a nitrogen atom, or CR 13 , 
         A4 represents a nitrogen atom, or CR 14 , 
         A5 represents a nitrogen atom, or CR 15 , 
         A6 represents a nitrogen atom, or CR 16 , 
         R 11 , R 13 , R 14 , R 15 , and R 16  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, 
         R 12  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom. 
         Group A is a group consisting of a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group, a C1-C6 alkylsulfanyl group, a C1-C6 alkylsulfinyl group, a C1-C6 alkylsulfonyl group, a C3-C6 cycloalkyl group (the C1-C6 alkoxy group, the C3-C6 alkenyloxy group, the C3-C6 alkynyloxy group, the C1-C6 alkylsulfanyl group, the C1-C6 alkylsulfinyl group, the C1-C6 alkylsulfonyl group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms), a cyano group, and a halogen atom. 
         Group B is a group consisting of a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C6 alkenyloxy group, a C3-C6 alkynyloxy group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, the C3-C6 alkenyloxy group, and the C3-C6 alkynyloxy group may be optionally substituted with one or more halogen atoms), a hydroxy group, a cyano group, a nitro group, and a halogen atom. 
         Group C is a group consisting of a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a cyano group, and a halogen atom.] 
         or its N-oxide or a salt thereof 
         to the resistant harmful arthropod or a habitat of the resistant harmful arthropod. 
       
     
     
         2 : The method according to  claim 1  wherein in the compound represented by formula (I), or its N-oxide or a salt thereof,
 Q represents a group represented by formula Q1 or a group represented by formula Q4, 
 A1 and A3 represents a nitrogen atom, 
 A2 represents an oxygen atom or NR 2 , 
 R 1  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), a nitro group, S(O) m R 10 , or a halogen atom, 
 R 2  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), a nitro group, S(O) n R 10a , a halogen atom, or a hydrogen atom. 
 
     
     
         3 : The method according to  claim 1  wherein in the compound represented by formula (I), or its N-oxide or a salt thereof,
 Q represents a group represented by formula Q1. 
 
     
     
         4 : The method according to  claim 1  wherein in the compound represented by formula (I), or its N-oxide or a salt thereof,
 Q represents a group represented by formula Q2 or a group represented by formula Q3, 
 A4 represents CR 14 , 
 A5 represents a nitrogen atom or CR 15 , 
 A6 represents a nitrogen atom, 
 R 1  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group {the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms}, a nitro group, S(O) m R 10 , or a halogen atom, 
 R 2  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), a nitro group, S(O) n R 10a , a halogen atom, or a hydrogen atom. 
 
     
     
         5 : The method according to  claim 1  wherein in the compound represented by formula (I), or its N-oxide or a salt thereof,
 Q represents a group represented by formula Q2. 
 
     
     
         6 : A compound represented by formula (II): 
       
         
           
           
               
               
           
         
         [wherein 
         R 21  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), S(O) p R 28  or a halogen atom, 
         R 22  represents a C1-C6 chain hydrocarbon group, a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 chain hydrocarbon group, the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), S(O) q R 29 , a halogen atom, or a hydrogen atom, 
         R 23 , R 25  and R 27  are identical or different from each other and each represents a fluorine atom or a hydrogen atom, 
         R 24  represents a C1-C6 alkoxy group which is substituted with one or more halogen atoms, or a fluorine atom, 
         R 26  represents a halogen atom, or a hydrogen atom, 
         R 28  and R 29  are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, and 
         p and q each independently is 0, 1 or 2] 
         or its N-oxide or a salt thereof. 
       
     
     
         7 : The compound according to  claim 6  wherein
 R 21  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a halogen atom, 
 R 22  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, 
 R 23 , R 25  and R 27  are identical or different from each other and each represents a fluorine atom or a hydrogen atom, 
 R 24  represents a C1-C6 alkoxy group which is substituted with one or more halogen atoms, or a fluorine atom, and 
 R 26  represents a halogen atom, or a hydrogen atom, 
 or its N-oxide, or a salt thereof. 
 
     
     
         8 : A compound represented by formula (II-a): 
       
         
           
           
               
               
           
         
         [wherein 
         R 21a  represents a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), or S(O) r R 28a , 
         R 22a  represents a C1-C6 alkoxy group, a C3-C7 cycloalkyl group (the C1-C6 alkoxy group, and the C3-C7 cycloalkyl group may be optionally substituted with one or more halogen atoms), S(O) 8 R 29a  or a halogen atom, 
         R 23a , R 25a  and R 27a  are identical or different from each other and each represents a halogen atom or a hydrogen atom, 
         R 24a  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group which is substituted with one or more halogen atoms, or a halogen atom, 
         R 26a  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, 
         R 28a  and R 29a  are identical or different from each other and each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, and 
         r and s each independently represents 0, 1 or 2] 
         its N-oxide or a salt thereof. 
       
     
     
         9 : A compound represented by formula (III): 
       
         
           
           
               
               
           
         
         [wherein 
         A combination of R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , and R 37  represents
 a combination wherein 
 R 31  and R 32  represent a chlorine atom, and R 33 , R 35  and R 37  represent a hydrogen atom, 
 R 34  represents a C1-C6 alkoxy group which is substituted with one or more halogen atoms, and 
 R 36  represents a halogen atom; or, 
 a combination wherein 
 R 31  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a bromine atom, 
 R 32  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a bromine atom, or a hydrogen atom, 
 R 33 , R 35  and R 37  are identical or different from each other and each represents a fluorine atom or a hydrogen atom, 
 R 34  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, or a halogen atom, and 
 R 36  represents a halogen atom or a hydrogen atom, and 
 
         R 38  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom], 
         or its N-oxide, or a salt thereof. 
       
     
     
         10 : A compound represented by formula (IV): 
       
         
           
           
               
               
           
         
         [wherein 
         R 41  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a halogen atom, 
         R 42  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, 
         R 43 , R 45  and R 47  are identical or different from each other and each represents a fluorine atom or a hydrogen atom, 
         R 44  represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom, and 
         R 46  represents a halogen atom or a hydrogen atom] 
         its N-oxide or a salt thereof. 
       
     
     
         11 : A composition comprising the compound according to  claim 6 , its N-oxide or a salt thereof, and an inert carrier. 
     
     
         12 : A composition which comprises one or more ingredients selected from the group consisting of Group (a), Group (b), Group (c) and Group (d), as well as the compound according to  claim 6 , or its N-oxide or a salt thereof:
 Group (a): a group consisting of an insecticidal ingredient, a miticidal ingredient, and a nematicidal ingredient;   Group (b): a fungicidal ingredient;   Group (c): a plant growth modulating ingredient; and   Group (d): a repellent ingredient.   
     
     
         13 : A method for controlling a resistant harmful arthropod which comprises applying an effective amount of the compound according to  claim 6 , its N-oxide or a salt thereof to the resistant harmful arthropod or a habitat where a resistant harmful arthropod lives. 
     
     
         14 : The method according to  claim 1  wherein the resistant harmful arthropod is the order of Hemiptera pest. 
     
     
         15 : The method according to  claim 1  wherein the resistant harmful arthropod is selected from an Aphididae family, a Delphacidae family, or an Aleyrodidae family. 
     
     
         16 : A seed or vegetative reproduction organ carrying an effective amount of the compound according to  claim 6 , its N-oxide or a salt thereof. 
     
     
         17 : A method for controlling a resistant harmful arthropod which comprises applying an effective amount of the composition according to  claim 12  to the resistant harmful arthropod or a habitat where a resistant harmful arthropod lives. 
     
     
         18 : A seed or vegetative reproduction organ carrying an effective amount of the composition according to  claim 12 .